Statistics for occurrence #1 of “Winter Hill” in chapter 7 of Historic leaves, volume 3, April, 1904 - January, 1905:

...Jaques, with wife and son. Mr. Jaques was one of the three sons of old Colonel Jaques who owned Ten Hills Farm. All the brothers have passed away, but one son and family still remain at the foot of Winter Hill . Uncle Edmund Tufts, so-called, lived nearly opposite, with his charming sister, Aunt Abbie. But they have both passed away, and the site of their little home is occupied by a block of buildings....
Max. Freq. Min. Freq.
Entity Corpus Doc Corpus Doc  
Winter Hill (Massachusetts, United States) 372 26 0 0 0 user votes
Winter Hill (Wyoming, United States) 80 12 0 0 0 user votes
Winter Hill (United Kingdom) 6 2 0 0 0 user votes
Winter Hill (Maine, United States) 4 0 0 0 0 user votes
Winter Hill (Massachusetts, United States) 0 0 0 0 0 user votes

† This entity has been selected by the automated classifier as the most likely match in this context. It may or may not be the correct match.